N-Iodosuccinimide → HCID 69077347、化合物

HRID 1916623ノート

反応式

HRID 1916623 の反応式
C([Li])CCC.[CH3:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:15][C:10]=2[N:9]=[CH:8]1.[I:22]N1C(=O)CCC1=O>CCCCCC.C1COCC1>[I:22][C:8]1[N:7]([CH3:6])[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:15][C:10]=2[N:9]=1

参加物

6

反応物 3

HCID 120273N-IodosuccinimideHCID 67362954HCID 67362954、化合物HCID 178418339Butyllithium

生成物 1

HCID 69077347HCID 69077347、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

0.80 mL (1.28 mmol) 1.6 M n-butyllithium solution in hexane are added to a solution, cooled to −75° C., of 250 mg (1.16 mmol) 1-methyl-5-pyrrolidin-1-ylmethyl-1H-benzimidazole in 8 mL THF. The reaction mixture is stirred for 10 min at this temperature and then 288 mg (1.28 mmol) N-iodosuccinimide in 5 mL THF are added. The cooling bath is removed and the reaction stirred for 1 h at RT. 12 mL 0.1 M HCl are added and the aqueous phase is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH/NH3 9:1:0.1).

後処理

  1. customThe cooling bath is removed
  2. stirringthe reaction stirred for 1 h at RT
  3. addition12 mL 0.1 M HCl are added
  4. extractionthe aqueous phase is extracted with EtOAc
  5. dry with materialThe organic phase is dried over MgSO4
  6. customThe purification

出典と根拠

ORDレコード
ord-203905a7d77046488e114cc9db773bb7
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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